Family-friendly holiday rentals in Hampshire County

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

The cozy clubhouse

Take a break and unwind at this peaceful cozy studio apartment with a private deck looking out over the garden and classic New England stone wall. Located on a quiet dead end street in the village of Haydenville. Not far from the local rail trail, hiking trails, and only a 13 minute drive to downtown Northampton. Very close to Look Park and Valley View Farm common wedding venues. A gateway to the Berkshires, with easy drive access to the Tanglewood music venue, Mount Greylock, and Mass MOCA.

Mill River Cottage (pet friendly!)

Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!

Serene 1-br suite on 75 acre horse property

Find your peaceful retreat in our 1-bedroom suite, situated on a serene 75-acre horse property with scenic nature trails. Enjoy a private entrance, dedicated workspace, and complimentary high-speed WiFi, making it an ideal haven for remote workers. Take in the picturesque views of our horse pastures, with up to 20 horses, right from your windows. Our property is nestled in the woods, about 1/3 mile from the main road. Located near Amherst, Hampshire, UMass, Smith, and Mt. Holyoke colleges.

Separate apt, 1 mile from downtown, 1 guest only

This is a private, clean, comfortable apartment with New pillow top mattress for 1 person with separate entrance in our new home. You will have the space to yourself. We are a mile from downtown near the bike path, the mill river, and Smith college. Private bathroom with a shower; kitchen basics: fridge, microwave, toaster, teapot, pour over coffee. Wifi and smart tv. Sunny with central air in the summer warm and cozy in the winter. Walk or ride a bike to town. We’re located in Village Hill.

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

E. Slate Carriage House

A comfortable studio in a converted 1890's Carriage House. Five minute walk to the center of "Noho." Close to cafes, events, public transportation, shops, Smith College. Reserved parking, private entrance. Efficient kitchen, laundry, large shower, AC/Heat. Wifi, coffee/tea provided. No shared walls. You may hear footsteps if there is a guest on the 2nd floor above. No road or pedestrian noise. 1-Queen bed. Studio is 430 sq. +/-. No TV. No smoking, vaping, burning incense/candles. Thank you.

Tiny House Farm Retreat: Mountain Views, Fire pit

The Tiny House at Milestone Farm is a cozy farm retreat loaded with modern conveniences. Designed as a romantic escape for couples to relax and enjoy the tranquility of the farmlands while viewing the beautiful Holyoke range. Take in the amazing views and watch the many facets of commercial farming during the growing season. Create your own menu using our fully stocked kitchen. Meat and seasonal produce available for purchase in our farmstand. Minutes from the center of Northampton.

Modern Comfort Meets Northampton’s Vibrant Charm

Experience the Best of Northampton! From vibrant nightlife to tranquil retreats, Northampton has something for everyone, and our newly renovated, two-bedroom duplex puts you right at the center of it all. Whether you’re catching live music, indulging in farm-to-table dining, or browsing unique local shops, every adventure is just steps away. Book your stay today and experience the perfect balance of comfort, convenience and charm in one of Northampton’s most highly rated homes!

Private Farm Studio Apartment

Our farm is a quiet, 5+ acre haven one mile from the center of Easthampton and 8-12 minutes from Smith College/Northampton. It's a great base from which to explore all the restaurants, cultural and outdoor activities offered in the beautiful Pioneer Valley. The private studio apartment is on the first level of our rustic farmhouse and offers a queen bed, kitchenette, living room, and bathroom. A sofabed is available for an extra $20 fee, please request this upon booking.

Large Studio – Walk to Town

IMPORTANT: Please read the full description about the eco-friendly policy and click the "CONTACT HOST" button, rather than making a reservation. I will respond very quickly to your request. Thank you for your consideration! A unique studio, loft-like, surrounded by beautiful gardens, a short walk to downtown and Smith College; perfect for visiting the five colleges, attending weddings, graduations, workshops, writing and research; close to hiking and bicycle trails.

Cozy Haven: Convenience & Charm

Welcome to our charming Florence, Massachusetts Airbnb! Only 10 minutes from downtown Northampton, our newly renovated property blends comfort, convenience, and natural beauty. Our location provides swift access to Northampton's vibrant heart. Within a 10-minute drive, you'll be amid bustling streets with eclectic shops, superb dining, and a lively arts scene. Explore boutiques, galleries, and cafes that define Northampton's creative and entertaining spirit.